4-Fluorobenzaldehyde → 4-(Benzenesulfonyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluorobenzaldehyde (6 g, 48 mmol), sodium benzenesulfinate (7.5 g, 4.6 mmol), and dimethylsulfoxide (30 mL) was heated at 100° C. for 20 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give a white solid. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was purified using flash chromatography (Analogix SuperFlash™ column, 15%-40% ethyl acetate in hexanes) to give 4.29 g (41%) of 4-(benzenesulfonyl)-benzaldehyde as a white solid.

Provenance & Evidence